Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(sp3)–H functionalization of amines†,Chemical Science

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Intramolecular hydride transfer onto arynes: redox-neutral and transition metal-free C(sp3)–H functionalization of amines†
Chemical Science ( IF 7.6 ) Pub Date : 2018-02-08 00:00:00 , DOI: 10.1039/c8sc00181b
Fahima I M Idiris ₁ , Cécile E Majesté ₁ , Gregory B Craven ₁ , Christopher R Jones ₁

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Transition metal-free intramolecular hydride transfer onto arynes is reported for the first time. This unique transformation is utilized in redox-neutral intermolecular α-functionalization reactions of different tertiary amines, generating C(sp³)–C(sp³/sp²/sp) bonds in a single synthetic operation. Deuterium labeling studies support initial cleavage of the α-C–H bond via intramolecular 1,5-hydride transfer onto the aryne, which leads to activation of a range of integrated pronucleophiles and ultimately affords a new approach to cross-dehydrogenative coupling reactions which utilize aryne intermediates.

中文翻译：

分子内氢化物转移到芳烃上：胺的氧化还原中性和无过渡金属的 C(sp3)–H 官能化†

首次报道了无过渡金属的分子内氢化物转移到芳烃上。这种独特的转化用于不同叔胺的氧化还原中性分子间α-官能化反应，在单一合成操作中生成C(sp ³ )–C(sp ³ /sp ² /sp)键。氘标记研究支持通过分子内 1,5-氢化物转移到芳炔上来初始裂解 α-C-H 键，这导致一系列整合的亲核试剂的激活，并最终提供了一种利用交叉脱氢偶联反应的新方法芳炔中间体。

更新日期：2018-02-08

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